4-(Trifluoromethyl)phenylboronic acid → 2-(3-Fluoro-4-hydroxyphenyl)-4-(4-trifluoromethylphenyl)quinolin-6-ol

HRID 7250

Reaktionsgleichung

Reaktionsgleichung von HRID 7250
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([F:20])[CH:14]=2)[CH:3]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1>>[F:20][C:15]1[CH:14]=[C:13]([C:4]2[CH:3]=[C:2]([C:26]3[CH:27]=[CH:28][C:23]([C:22]([F:33])([F:32])[F:21])=[CH:24][CH:25]=3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=3)[N:5]=2)[CH:18]=[CH:17][C:16]=1[OH:19]

Komponenten

3

Edukt 2

HCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 1354779434-Bromo-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

Produkt 1

HCID 1354401272-(3-Fluoro-4-hydroxyphenyl)-4-(4-trifluoromethylphenyl)quinolin-6-olAusbeute 76 %

Versuchsvorschrift

This compound was prepared from 6b using 4-trifluoromethylphenylboronic acid according to method P. Yellow crystals; Yield: 76%; mp 299–300° C.; 1H-NMR (400 MHz, DMSO-d6) δ 7.07 (dd, J=8.8, 8.8 Hz, 1H), 7.12 (d, J=2.6 Hz, 1H), 7.31 (dd, J=9.1, 2.6 Hz, 1H), 7.40 (d, J=8.0 Hz, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.82 (s, 1H), 7.94 (dd, J=8.4, 2.1 Hz, 1H), 7.96 (d, J=9.0 Hz, 1H), 8.07 (dd, J=13.0, 2.0 Hz, 1H), 9.91 (s, 1H), 10.21 (s, 1H); 19F-NMR (400 MHz, DMSO-d6) δ −136.58 (dd, J=13.2, 9.3 Hz), −61.43 (s); MS (ESI) m/z 398 ([M−H]−), 400 ([M+H]+); Anal. Calcd for C22H13F4NO2: C: 66.17, H: 3.28, N: 3.51. Found: C: 66.09, H: 3.41, N: 3.45.

Quellen und Nachweise

ORD-Eintrag
ord-3b1a5620622c48788ea58af1537cfdc0
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084276B2

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